Ted Kennedy
Tyson and Hill have not made a success of their lives after committing crimes. Don King and Marion Barry are debatable. If the sole measure for the OP is ex-cons who made a lot of money, the doors are wide open.
How about actor Mark Wahlberg? He was in the adult prison system in Massachusetts as a 17 year old after being charged with attempted murder. He had a series of arrests for violent assaults, but after that prison stint found a way to re-channel his energies. After making a couple of hit records, he turned to acting, and got an Oscar nomintaion this year.
Ron LeFlore was an ex-con who went on to be an all-star outfielder with the Detroit Tigers and Chicago White Sox.
William Sydney Porter adopted the pen name O. Henry so that he could get his stories published while serving a five-year sentence for embezzlement. His peak came in the years after his release when he was writing weekly stories for the New York Sunday World.
Martin Luther King was in prison more than once, but I suppose he qualifies as a political prisoner, not a crook. Dostoyevsky would be in the same boat, and countless others.
And the grown-up Anne Perry was “discovered” after Peter Jackson made the movie Heavenly Creatures. There was curiousity about what became of the two young women. It turned out that the young woman played by Kate Winslet, grew up, moved to the UK and became a mystery writer.
Heavenly Creatures is a good movie, by the way, for anyone who hasn’t seen it.
Issei Sagawa, who could most charitably be described as a “rogue gourmet” went on to a far amount of fame and success, appearing in several movies, publishing several books (including a cookbook), and frequently getting invited as a talk show guest.
http://www.crimelibrary.com/serial_killers/weird/sagawa/1.html
El Lute. A two-bit analphabet thief who ended up becoming a published author and living a comfortable middle-class life with wife, kids etc. Given how low in the social scale he’d started, it’s comparable to being born to a bag lady and later living in a gated community’s largest house (and not as the handyman).
Damn you, Sublight, you beat me to it. I like citing that little slimeball as an example of the Japanese love of depravity.
Kevin Mitnick started a security consulting company, wrote a couple of books (check the Recent Activity section), and is probably making a very comfortable living now.
Until I checked the dictionary I was almost afraid to ask what he was stealing.
Thank you, Nava, I learned a new word today.
John Singleton Mosby was convicted of “unlawful shooting”, and spent some time in jail before receiving a pardon. He went on to distinguish himself in the Confederate Army, and then in the U.S. government after the war…
This post I like!
The key is to not ever get caught. Me? I’m doing just fine, thanks.
Well, it bums me out when a furriner has a better vocabulary than me. 
< Sesame Street > …Psst! Ya wanna buy a 'Q"? < /SS >
Actor Charles S. Dutton did time for murder.
He did time for stabbing someone in a fight; I don’t know what the actual charge was.
Duane “Dog” Chapman, the bounty hunter, did time for murder. IIRC, he was running with a biker gang at the time of his arrest and he has always claimed that the murder was committed by another member of the gang. He was paroled after five years or so.
He was an analphabet–someone who doesn’t know the alphabet–someone who was illiterate–who was a thief.
He didn’t steal alaphabets.
Ian Shrager is ridiculously successful
Oliver North
Danny Trejo spent a lot of time in and out of jail for robbery and drug offenses before getting himself straightened out and becoming a rather successful character actor.
Lenny “The Guvnor” or “the hardest man in Britain” McLean did time in detention centres and was charged with assault but cleared of manslaughter as an adult. Had his fingers in a lot of criminal dealings, though.
He was the probably the most famous unlicensed boxer, was incredible to watch in the ring, a seething ball of aggression. He was known of late for playing Barry the Baptist in Lock Stock and Two Smoking Barrels, released just two weeks after his death. Moderately good 'auto’biography, the Guvnor.
Let’s not overlook Kevin Trudeau, TV pitchman and sleaze purveyor extraordinaire, whose shady past includes a nearly two-year stay with Uncle Sam for credit card fraud, but who recently had a bestselling book (“Natural Cures They Don’t Want You To Know About”).
Copies were snapped up by the sort of people who also believe that They are suppressing an additive that lets you get 200 miles per gallon of gas, that planes did not crash into the Pentagon and WTC and that Tom Cruise’s behavior is the result of alien abduction.
Well, one out of three ain’t bad. :dubious:
Tony Sirico, Paulie from The Sopranos , is a convicted stick-up man who was last jailed in 1972.
According to IMDB, he’s appeared 40 times on-screen as a gangster and 5 as a crooked cop.
For him, make-believe crime has paid much better than the real thing.